123695-95-4

Upstream product

• 17639-93-9 2-chloro-propionic acid methyl ester 
• 106-47-8 4-chloro-aniline 
• 600-22-6 pyruvic acid methyl ester 
• 186581-53-3 diazomethane 
• 83442-61-9 2-(4-chlorophenylamino)propanoic acid 

Downstream Products

• 103678-25-7 (R)-2-(4-Chloro-phenylamino)-propionic acid 
• 103678-25-7 (2S)-2-[(4-chlorophenyl)amino]propanoic acid 
• 199679-82-8 (2R)-(4-chlorophenyl)alanine methyl ester 

Relevant academic research and scientific papers

Enantioselective hydrolysis of some 2-aryloxyalkanoic acid methyl esters and isosteric analogues using a penicillin G acylase-based HPLC monolithic silica column

A technique based on liquid chromatography has been developed to facilitate studies of enantioselectivity in penicillin G acylase (PGA)-catalyzed hydrolysis of some 2-aryloxyalkanoic acid methyl esters and isosteric analogues. PGA was covalently immobilized on an aminopropyl monolithic silica support to create an immobilized HPLC-enzyme reactor. Two sets of experimental data were drawn to calculate the enantioselectivity (E) of the kinetically controlled enantiomer-differentiating reaction, the degree of substrate conversion and the enantiomeric excess of the product. The developed enzymatic reactor was coupled through a switching valve to an achiral analytical column for separation and quantitation of the hydrolysis products. The enantiomeric excess was determined off-line on a PGA-chiral stationary phase. In this way, highly precise E values were determined. A computational study related to the hydrolysis of the considered racemic esters was also carried out in order to unambiguously clarify both the substrate specificity and the enantioselectivity displayed by PGA.

Catalytic reductive N-alkylation of anilines. Application to the synthesis of N-aryl aminoacid precursors

Different anilines have been monoalkylated by reductive alkylation using ketones and α-ketoesters as alkylating agents with good isolated yields. This provided access to aminoacid derivatives. Diastereoselective experiments were also performed.

The Stereochemical Investigation of 3-Aryl-.4-methyl-1,2,3-oxathiazolidine 2-oxides Using NMR

The title compounds were prepared by the reaction of the corresponding N-2-hydroxyisopropylanilines with thionyl chloride in the presence of triethylamine, and their pmr and cmr spectra were examined.On the basis of the chemical shifts due to the γ and δ-effects, the stereochemical structures are discussed.